US20200381629A1 - Heterocyclic compound and organic light emitting element comprising same - Google Patents
Heterocyclic compound and organic light emitting element comprising same Download PDFInfo
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- US20200381629A1 US20200381629A1 US16/496,776 US201816496776A US2020381629A1 US 20200381629 A1 US20200381629 A1 US 20200381629A1 US 201816496776 A US201816496776 A US 201816496776A US 2020381629 A1 US2020381629 A1 US 2020381629A1
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- substituted
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- light emitting
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 72
- 239000000463 material Substances 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 239000011368 organic material Substances 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 15
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 14
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 238000012546 transfer Methods 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 4
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- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 88
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- 238000002360 preparation method Methods 0.000 description 32
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- 0 Cc1ccccc1-c(c(C)c1*2c3ccc4[U]c(cc(cc5)-c6nc(-c7ccccc7)nc(-c7ccccc7)n6)c5-c4c3)ccc1-c1c2cccc1 Chemical compound Cc1ccccc1-c(c(C)c1*2c3ccc4[U]c(cc(cc5)-c6nc(-c7ccccc7)nc(-c7ccccc7)n6)c5-c4c3)ccc1-c1c2cccc1 0.000 description 27
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- 125000006267 biphenyl group Chemical group 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- AYHGAQGOMUQMTR-UHFFFAOYSA-N BrC1=CC=C(C2=NC(C3=CC=CC=C3)=NC(C3=CC=CC=C3)=N2)C=C1 Chemical compound BrC1=CC=C(C2=NC(C3=CC=CC=C3)=NC(C3=CC=CC=C3)=N2)C=C1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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2018
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US20200266355A1 (en) * | 2017-09-15 | 2020-08-20 | Heesung Material Ltd. | Heterocyclic compound and organic light emitting element comprising same |
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US20210057651A1 (en) * | 2019-08-23 | 2021-02-25 | Lt Materials Co., Ltd. | Organic light emitting device, method for manufacturing same and composition for organic material layer |
US11785844B2 (en) * | 2019-08-23 | 2023-10-10 | Lt Materials Co., Ltd. | Organic light emitting device, method for manufacturing same and composition for organic material layer |
Also Published As
Publication number | Publication date |
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TW202309246A (zh) | 2023-03-01 |
KR20180108425A (ko) | 2018-10-04 |
KR101915712B1 (ko) | 2018-11-06 |
EP3611173B1 (en) | 2021-07-28 |
KR102527349B1 (ko) | 2023-05-02 |
TWI703201B (zh) | 2020-09-01 |
EP3604297A4 (en) | 2020-11-25 |
EP3611173A4 (en) | 2020-12-02 |
TW201840815A (zh) | 2018-11-16 |
JP7298909B2 (ja) | 2023-06-27 |
US11387418B2 (en) | 2022-07-12 |
CN110520420A (zh) | 2019-11-29 |
TWI812526B (zh) | 2023-08-11 |
EP3611173A1 (en) | 2020-02-19 |
KR20190010693A (ko) | 2019-01-30 |
EP3604297A1 (en) | 2020-02-05 |
EP3604297B1 (en) | 2022-11-30 |
KR20180108427A (ko) | 2018-10-04 |
KR20230065940A (ko) | 2023-05-12 |
TWI794218B (zh) | 2023-03-01 |
CN110573506A (zh) | 2019-12-13 |
TW201840817A (zh) | 2018-11-16 |
US20200119285A1 (en) | 2020-04-16 |
JP2020514385A (ja) | 2020-05-21 |
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